9, 10-epoxyoctadecanol and process for its preparation



Patented Nov. 26, 1946 V v UNITED STATES PATENT OFFICE 9,10-EPOXYOCTADECANOL AND PROCESS FOR ITS PREPARATION Daniel Swern, Philadelphia, Pa., assignor to United States of America, as represented by the Secretary of Agriculture No Drawing. Application December 8, 1944, Serial No. 567,297

2 Claims. (Cl. 260348) (Granted under the act of March 3, 1883, as amended April 30, 1928; 370 0. G. 757) This application is made under the act of March added 274 grams of oleyl alcohol. The solution 3, 1883, as amended by the act of April 30, 1928, is then allowed to stand for about 40 hours at and the invention herein described, if patented, room temperature and then cooled to about 25 may be manufactured and used by or for the C. The precipitate obtained is then filtered of! Government of the United States of America for 5 and dried. It is found to weigh about 247 grams governmental purposes without the payment to (89% yield) and has a melting point of about me of any royalty th 54 C. to 555 C. Analysis of this material for This invention relates to oxidation products of epoxy oxygen gives the following results: olefinic alcohols and, in particular, to the oxida- Calculated for 9,10-epoxyoctadecano1: 5.62% tion product of oleyl alcohol and perbenzoic acid, 10 epoxy oxygen; found: 5.57% epoxy oxygen. v and has as its object the production of 9,10- The new compound, 9,10-epoxyoctadecanol, is epoxyoctadecanol. useful as an intermediate in organic synthesis, According to the invention, oleyl alcohol and particularly in e fields f plastics and surfaceperbenzoic acid are reacted together to form :1 active agents. new compound, namely 9,10-epoxyoctadecanol, 15 H g thus described the invention. What is as illustrated by the following equation: claimed 15! 1. 9,10-epoxyoctadecanol. cmwna gg g gggm m fl igz gzgg g l 2. A process of preparing 9,10-epoxy0ctadeca.

nol, comprising reacting oleyl alcohol with a solu- Cmwm),CH CH(QH,),CH,OH (35.00011 0 tion of perbenzoic acid in acetone at about 0 C. to 5 C., then permitting the resulting solution to (9,10-epoxyoctadecanol) (Benzoic acid) stand for about 40 hours at about room temperature, then cooling this solution to about 25 C. The follow an example of the manner of to form a precipitate which comprises mainly pr pa f c0mp0 I 25 9,10-epoxyoctadecanol, and then isolating the To 3140 ml. of acetone at about 0 C. to 5 C. formed precipitate. and containing 138 grams of perbenzoic acid is DANIEL SWERN. 

